sodium perborate in acetic acid T=60 - 115°C; 1 h;

sodium hydroxide in ethanol

1: 1) sodium nitrite, aq. HCl 2) KI, CuI / 1) under 0 deg C 2) water, 2 h reflux 2: 100 percent / NaOH, CuI / H2O / 8 h / Heating 3: 99 percent / 1) lithium diisopropylamide / tetrahydrofuran; various solvent(s) / 1) -5 to -15 deg C, 40 min. 2) warming to 10 deg C, 3 h 4: 98 percent / polyphosphoric acid, water / 0.5 h / 140 °C 5: 97 percent / NaOH, NaBH4 / ethanol; H2O / 2 h / Ambient temperature 6: 86 percent / conc. H2SO4 / acetic acid / 1 h / 55 - 75 °C 7: 95 percent / sodium perborate tetrahydrate / acetic acid / 1 h / 60 - 115 °C View Scheme

1: 96 percent / Cu2O / quinoline / 0.75 h / 185 - 190 °C 2: 99 percent / 1) lithium diisopropylamide / tetrahydrofuran; various solvent(s) / 1) -5 to -15 deg C, 40 min. 2) warming to 10 deg C, 3 h 3: 98 percent / polyphosphoric acid, water / 0.5 h / 140 °C 4: 97 percent / NaOH, NaBH4 / ethanol; H2O / 2 h / Ambient temperature 5: 86 percent / conc. H2SO4 / acetic acid / 1 h / 55 - 75 °C 6: 95 percent / sodium perborate tetrahydrate / acetic acid / 1 h / 60 - 115 °C View Scheme

1: 100 percent / NaOH, CuI / H2O / 8 h / Heating 2: 99 percent / 1) lithium diisopropylamide / tetrahydrofuran; various solvent(s) / 1) -5 to -15 deg C, 40 min. 2) warming to 10 deg C, 3 h 3: 98 percent / polyphosphoric acid, water / 0.5 h / 140 °C 4: 97 percent / NaOH, NaBH4 / ethanol; H2O / 2 h / Ambient temperature 5: 86 percent / conc. H2SO4 / acetic acid / 1 h / 55 - 75 °C 6: 95 percent / sodium perborate tetrahydrate / acetic acid / 1 h / 60 - 115 °C View Scheme

1: 99 percent / 1) lithium diisopropylamide / tetrahydrofuran; various solvent(s) / 1) -5 to -15 deg C, 40 min. 2) warming to 10 deg C, 3 h 2: 98 percent / polyphosphoric acid, water / 0.5 h / 140 °C 3: 97 percent / NaOH, NaBH4 / ethanol; H2O / 2 h / Ambient temperature 4: 86 percent / conc. H2SO4 / acetic acid / 1 h / 55 - 75 °C 5: 95 percent / sodium perborate tetrahydrate / acetic acid / 1 h / 60 - 115 °C View Scheme

1: 97 percent / NaOH, NaBH4 / ethanol; H2O / 2 h / Ambient temperature 2: 86 percent / conc. H2SO4 / acetic acid / 1 h / 55 - 75 °C 3: 95 percent / sodium perborate tetrahydrate / acetic acid / 1 h / 60 - 115 °C View Scheme

1: 86 percent / conc. H2SO4 / acetic acid / 1 h / 55 - 75 °C 2: 95 percent / sodium perborate tetrahydrate / acetic acid / 1 h / 60 - 115 °C View Scheme

1: 98 percent / polyphosphoric acid, water / 0.5 h / 140 °C 2: 97 percent / NaOH, NaBH4 / ethanol; H2O / 2 h / Ambient temperature 3: 86 percent / conc. H2SO4 / acetic acid / 1 h / 55 - 75 °C 4: 95 percent / sodium perborate tetrahydrate / acetic acid / 1 h / 60 - 115 °C View Scheme

pyridine; sodium tetrahydroborate; chloroformic acid ethyl ester 1) tetrahydrofuran, 1 h 2) water, tetrahydrofuran, 20 deg C, 1 h; Yield given. Multistep reaction;